Methyl 4-Formylbenzoate → HCID 20071004, compound

HRID 981807Notes

Reaction equation

HRID 981807 reaction equation
[PH4+].[Li][CH2:3][CH2:4][CH2:5][CH3:6].[CH:7]([C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)=O>O1CCCC1>[CH3:6][C:5]1[C:13]([CH2:12]/[CH:17]=[CH:7]/[C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[CH:3][C:4]2[CH2:5][CH2:6][C:9]([CH3:18])([CH3:7])[CH2:10][CH2:11][C:3]=2[CH:4]=1

Participants

5

Reactant 3

HCID 15294Methyl 4-FormylbenzoateHCID 5460504PhosphoniumHCID 178418339Butyllithium

Product 1

HCID 20071004HCID 20071004, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In analogy to Example 1B (1st paragraph), from 6,7,8,9-tetrahydro-α,3,7,7-tetramethyl-5H-benzocycloheptene-2-methanol, there is obtained the corresponding phosphonium salt. 5.30 g of the phosphonium salt are suspended in 35 ml of tetrahydrofuran and deprotonized at 0° with 9.0 ml of 1.4M nBuLi (hexane) After 30 minutes, 2 30 g of methyl 4-formylbenzoate are added thereto and the mixture is stirred at room temperature for an additional 2 hours. The mixture is poured on to ice-water, extracted with Et2O, washed with water, dried and evaporated. Chromatography on silica gel (low-boiling petroleum ether/AcOEt=93/3), followed by crystallization from n-hexane, yields 560 mg of methyl p-[(E)-(6,7,8,9-tetrahydro-3,7,7-trimethyl-5H-benzocyclohepten-2-yl) propenyl]benzoate of m.p. 59°-60°.

Workup

  1. extractionextracted with Et2O
  2. washwashed with water
  3. customdried
  4. customevaporated
  5. customChromatography on silica gel (low-boiling petroleum ether/AcOEt=93/3), followed by crystallization from n-hexane

Sources & evidence

ORD record
ord-491d8052aa10401d8131021bc381d7ca
Source dataset
uspto-grants-1991_02
Patent number
US04992574

Reaction notes

Loading…